2-(6-ethyl-2-methyl-1-(4-(methylsulfonyl)benzyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)acetic acid

ID: ALA4086277

PubChem CID: 137643575

Max Phase: Preclinical

Molecular Formula: C20H22N2O4S

Molecular Weight: 386.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccc2c(CC(=O)O)c(C)n(Cc3ccc(S(C)(=O)=O)cc3)c2n1

Standard InChI:  InChI=1S/C20H22N2O4S/c1-4-15-7-10-17-18(11-19(23)24)13(2)22(20(17)21-15)12-14-5-8-16(9-6-14)27(3,25)26/h5-10H,4,11-12H2,1-3H3,(H,23,24)

Standard InChI Key:  QKTZDUXKWPIHAY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   24.2887   -7.1112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8843   -6.4055    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.4753   -7.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0540   -3.9629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7150   -3.4822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4598   -2.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4925   -3.7336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9373   -2.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7504   -2.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2279   -1.4587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0860   -2.8670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0553   -4.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7637   -5.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7614   -6.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4690   -6.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1770   -5.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1730   -5.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4649   -4.7746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5924   -5.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3915   -3.4844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6443   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1018   -2.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3063   -2.2764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0563   -3.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6005   -3.6537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2575   -3.2261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7087   -2.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
 20  4  1  0
  4  5  1  0
  5  6  2  0
  6 21  1  0
  5  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 16  2  1  0
  2 19  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 24 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4086277

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 386.47

Molecular Weight (Monoisotopic): 386.1300

AlogP: 2.99

#Rotatable Bonds: 6

Polar Surface Area: 89.26

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.46

CX Basic pKa: 3.80

CX LogP: 2.19

CX LogD: -0.32

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.70

Np Likeness Score: -1.20

References

1. Sandham DA, Barker L, Brown L, Brown Z, Budd D, Charlton SJ, Chatterjee D, Cox B, Dubois G, Duggan N, Hall E, Hatto J, Maas J, Manini J, Profit R, Riddy D, Ritchie C, Sohal B, Shaw D, Stringer R, Sykes DA, Thomas M, Turner KL, Watson SJ, West R, Willard E, Williams G, Willis J..  (2017)  Discovery of Fevipiprant (NVP-QAW039), a Potent and Selective DP2 Receptor Antagonist for Treatment of Asthma.,  8  (5): [PMID:28523115] [10.1021/acsmedchemlett.7b00157]

Source

Source(1):

• Scientific Literature